EP0036244A1 - Herbicidal compositions comprising 1-(3,4-dichloro-benzyl)imidazole-N,N'-dimethyl-4,5-dicarboxamide - Google Patents

Herbicidal compositions comprising 1-(3,4-dichloro-benzyl)imidazole-N,N'-dimethyl-4,5-dicarboxamide Download PDF

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Publication number
EP0036244A1
EP0036244A1 EP81300430A EP81300430A EP0036244A1 EP 0036244 A1 EP0036244 A1 EP 0036244A1 EP 81300430 A EP81300430 A EP 81300430A EP 81300430 A EP81300430 A EP 81300430A EP 0036244 A1 EP0036244 A1 EP 0036244A1
Authority
EP
European Patent Office
Prior art keywords
isoproturon
metoxuron
imidazole
dimethyl
dicarboxamide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP81300430A
Other languages
German (de)
English (en)
French (fr)
Inventor
Richard Henry Hewett
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by May and Baker Ltd filed Critical May and Baker Ltd
Publication of EP0036244A1 publication Critical patent/EP0036244A1/en
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Definitions

  • ED90 effective dose kg a.i./ha giving 90% growth reduction
  • Tween 20 wetting agent was added to each spray suspension to give a concentration of 0.01%.
  • the aqueous concentrate was then diluted by adding 10 ml of distilled water, 0.5 ml of a 1% aqueous solution of Tween 20, and making up to 50 ml.
  • the powders were suspended in water and diluted to 50 ml in the same way as were the Compound A suspensions.
  • ED90 effective dose kg a.i./ha giving 90% growth reduction
  • Machine a motorized small plot sprayer using 5 x 8002 tee jets each at 50 cm spacing at 30 p.s.i. (2.1 kgf/cm 2 ) giving 248.2 1/ha in low gear.
  • Soil condition at spraying ground firm with even tilth, surface wet.
  • Crop head counts in 2 x 1/2 m 2 quadrats/plot were initially carried out to indicate whether differences in potential yield were apparent in these treatments. Final yields per treatment were carried out by combine harvester. The yield and percentage moisture of grain was recorded for each plot and the weights were corrected for moisture content. Machine for combining:
  • Machine a motorized small plot sprayer using 5 x 8002 tee jets each at 50 cm spacing at 30 p.s.i. (2.1 kgf/cm2) giving 252.6 1/ha in low gear.
  • Crop head counts were carried out in each plot as for site 1. Yield estimations by combine harvester were not carried out at this site.
  • Crop winter barley (Maris Otter)
  • Machine a motorized small plot sprayer using 5 x 80015 tee jets each at 50 cm spacing at 30 p.s.i. (2.1 kgf/cm ) giving 197 1/ha in low gear.
  • Soil type not known.
  • Soil condition at spraying soil surface up to 1/4" deep was dry, beneath that fairly moist. Tilth - cloddy with cap.
  • Machine for combining also as for site 1.
  • compositions suitable for herbicidal use comprising (a) isoproturon and/or metoxuron and (b) l-(3,4-dichlorobenzyl)imidazole-N,N'- dimethyl-4,5-dicarboxamide (Compound A) in proportions of 4:1 to 1:1 of (a) to (b) [preferably 2:1 to 1:1 of (a) to (b)] in association with, and preferably homogeneously dispersed in, one or more compatible herbicidally-acceptable diluents or carriers (i.e.
  • compositions are used in a broad sense to include not only compositions which are ready for use as herbicides but also concentrates which must be diluted before use.
  • the compositions contain from 0.05 to 90% by weight of isoproturon and/or metoxuron and Compound A.
  • the herbicidal compositions may contain both a diluent or carrier and a surface-active (e.g. wetting, dispersing, or emulsifying) agent.
  • Surface-active agents which may be present in herbicidal compositions of the present invention may be of the ionic or non-ionic types, for example sulphoricinoleates, quaternary ammonium derivatives, products based on condensates or ethylene oxide with nonyl- or octyl-phenols, or carboxylic acid esters of anhydrosorbitols which have been rendered soluble by etherification of the free hydroxy groups by condensation with ethylene oxide, alkali and alkaline earth metal salts of sulphuric acid esters and sulphonic acids such as dinonyl- and dioctyl-sodium sulphonosuccinates and alkali and alkaline earth metal salts of high molecular weight sulphonic acid derivatives such as sodium and calcium lignos
  • suitable solid diluents or carriers are aluminium silicate, talc, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, adsorbent carbon black and clays such as kaolin and bentonite.
  • the solid compositions are preferably prepared by grinding the isoproturon and/or metoxuron and Compound A with solid diluents or by impregnating the solid diluents or carriers with solutions of the isoproturon and/or metoxuron and Compound A in volatile solvents, evaporating the solvents and, if necessary, grinding the products so as to obtain powders.
  • Granular formulations may be prepared by absorbing the isoproturon and/or metoxuron and Compound A (dissolved in volatile solvents) onto the solid diluents or carriers in granular form and evaporating the solvents, or by granulating compositions in powder form obtained as described above.
  • Solid herbicidal compositions, particularly wettable powders may contain wetting or dispersing agents (for example of the types described above), which may also, when solid, serve as diluents or carriers.
  • Liquid compositions according to the invention may take the form of aqueous, organic or aqueous-organic solutions, suspensions and emulsions which may incorporate a surface-active agent.
  • Suitable liquid diluents for incorporation in the liquid compositions include water, acetophenone, cyclohexanone, isophorone, toluene, xylene and mineral, animal and vegetable oils (and mixtures of these diluents).
  • Wettable powders and liquid compositions in the form of concentrates may be diluted with water or other suitable diluents, for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • liquid compositions of the isoproturon and/or metoxuron and Compound A may be used in the form of self-emulsifying concentrates containing the active substances dissolved in the emulsifying agents or in solvents containing emulsifying agents compatible with the active substances, the simple addition of water to such concentrates producing compositions ready for use.
  • herbicidal compositions according to the present invention may comprise from 0.05% to 10% of surface active agent.
  • Herbicidal compositions according to the present invention may also contain, if desired, conventional adjuvants such as adhesives, protective colloids, thickeners, penetrating agents, stabilizers, sequestering agents, anti-caking agents, colouring agents and corrosion inhibitors. These adjuvants may also serve as carriers or diluents.
  • Preferred herbicidal compositions according to the present invention are aqueous suspension concentrates which comprise from 10 to 70% w/v of isoproturon and/or metoxuron and Compound A, from 2 to 10% w/v surface-active agent, from 0.1 to 5% w/v of thickener and from 15 to 87.9% by volume of water, and wettable powders which comprise from 10 to 90% w/w of isoproturon and/or metoxuron and Compound A, from 2 to 10% w/w of surface-active agent and from 10 to 88% w/w of diluent or carrier.
  • Herbicidal compositions according to the present invention may also comprise the isoproturon and/or metoxuron and Compound A in association with, and preferably homogeneously dispersed in, one or more pesticidally active compounds and, is desired, one or more compatible pesticidally acceptable diluents or carriers, surface-active agents and conventional adjuvants as hereinbefore described, which may be prepared by the application of conventional techniques for the preparation of compositions suitable for herbicidal use, for example as hereinbefore described for the preparation of compositions comprising isoproturon and/or metoxuron and Compound A.
  • Examples of compounds which may be included in, or used in conjunction with, the herbicidal compositions of the present invention include especially herbicides with good activity by post-emergence application against Galium aparine, as hereinbefore described and, in particular, mecoprop and its metal, e.g. sodium or potassium, and amine salts and esters, in the proportions hereinbefore specified, or other herbicides, for example:
  • Pesticidally active compounds and other biologically active materials which may be included in, or used in conjunction with, the herbicidal compositions of the present invention, for example those hereinbefore mentioned, and which are acids, may, if desired, be utilised in the form of conventional derivatives, for example alkali metal and amine salts and esters.
  • compositions of the invention may be made up as an article of manufacture comprising isoproturon and/ or metoxuron and 1-(3,4-dichlorobenzyl)imidazole-N,N'- dimethyl-4,5-dicarboxamide (Compound A) and optionally other pesticidally active compounds as hereinbefore described and especially herbicides with good activity by post-emergence application against Galium aparine and, in particular, mecoprop and its metal, e.g.
  • a herbicidal composition as hereinbefore described and preferably a herbicidal concentrate which must be diluted before use, comprising isoproturon and/or metoxuron and Compound A within a container for the aforesaid isoproturon and/or metoxuron and Compound A or a said herbicidal composition, and instructions physically associated with the aforesaid container setting out the manner in which the aforesaid isoproturon and/or metoxuron and Compound A or herbicidal composition contained therein is to be used to control the growth of weeds.
  • the containers will normally be of the types conventionally used for the storage of chemical substances which are solids at normal ambient temperatures and herbicidal compositions, particularly in the form of concentrates, for example cans and drums of metal, which may be internally-lacquered, and plastics materials, bottles of glass and plastics materials and, when the contents of the container is a solid, for example granular herbicidal compositions, boxes, for example of cardboard, plastics materials and metal, or sacks.
  • the containers will normally be of sufficient capacity to contain amounts of the imidazole derivatives or herbicidal compositions sufficient to treat at least one acre of ground to control the growth of weeds therein but will not exceed a size which is convenient for conventional methods of handling.
  • the instructions will be physically associated with the container, for example by being printed directly thereon or on a label or tag affixed thereto.
  • the directions will normally indicate that the contents of the container, after dilution if necessary, are to be applied to control the growth of weeds at rates of application between 0.25 kg and 2 kg each of isoproturon and/or metoxuron and Compound A per hectare in the manner and for the purposes hereinbefore described.
  • An aqueous suspension concentrate formulation containing:- was prepared, by intimately mixing the ingredients and grinding in a ball-mill, for use at a rate of 4 litres in 200 litres of water/ha to control a wide spectrum of grass and broad-leafed weeds as hereinbefore described in cereal crops.
  • An aqueous suspension concentrate formulation was formed from:- by intimately mixing the ingredients and grinding in a ball-mill for 24 hours.
  • the concentrate thus obtained may be dispersed in water and applied at a rate of 5 litres of aqueous suspension concentrate in 300 litres of spray fluid per hectare to control the growth of a wide spectrum of broad-leafed weeds and grasses as hereinbefore described, for example Veronica persica, Viola arvensis, Stellaria media, Polygonum aviculare, Galiumaparine, Matricaria inodora and Alopecurus myosuroides, by post-emergence application in an emerged crop of winter wheat.
  • a wettable powder was formed from:- by mixing the ingredients and grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at a rate of 5 kg of wettable powder in 200 litres of spray fluid per hectare to control the growth of a wide spectrum of broad-leafed weeds and grasses as hereinbefore described, for example Veronica persica, Viola arvensis, Stellaria media, Matricaria inodora, Polygonum spp., and Alopecurus myosuroides, by post-emergence application in an emerged crop of winter wheat.
  • a wettable powder was formed from:- by mixing the ingredients and grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at an application rate of 2.5 kg of wettable powder in 200 litres of spray fluid per hectare to control the growth of a wide spectrum of broad-leafed weeds and grasses as hereinbefore described, for example Veronica persica, Viola arvensis, Stellaria media, Matricaria inodora, Polyqonum spp., and Poa annua, by post-emergence application in an emerged crop of winter wheat.
  • a wettable powder was formed from:- by mixing the ingredients and grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at application rates of from 1 to 8 kg of wettable powder in 200 to 1000 litres of spray fluid per hectare to control the growth of a wide spectrum of broad-leafed weeds and grasses as hereinbefore described by post-emergence application in an emerged crop of winter wheat, the lower application rates of from 1 to 3 kg/ha being particularly suitable for controlling the growth of seedling broad-leafed weeds and grasses, for example Stellaria media, Matricaria inodora, Veronica persica, Viola arvensis, Polygonum spp., and Poa annua, and the higher application rates being particularly suitable for controlling the growth of established broad-leafed weeds and grasses, for example Stellaria media, Matricaria inodora, Veronica persica, Viola arvensis, Polygonum spp., Alopecurus myo
  • aqueous suspension concentrate was formed from:- by intimately mixing the ingredients and grinding in a ball-mill for 24 hours.
  • the concentrate thus obtained may be dispersed in water and applied at an application rate of 5 litres of aqueous suspension concentrate in 300 litres of spray fluid per hectare to control the growth of a wide spectrum of broad-leafed weeds and grasses as hereinbefore described, for example Veronica persica, Viola arvensis, Stellaria media, Polygonum aviculare, Galium aparine, Matricaria inodora and Alopecurus myosuroides, by post-emergence application in an emerged crop of winter wheat.
  • aqueous suspension concentrate was formed from:- by intimately mixing the ingredients and grinding in a ball-mill for 24 hours.
  • the concentrate thus obtained may be dispersed in water and applied at an application rate of 10 litres of aqueous suspension concentrate in 300 litres of spray fluid per hectare to control the growth of a wide spectrum of broad-leafed weeds and grasses as hereinbefore described, for example Veronica persica, Viola arvensis, Stellaria media, Polygonum aviculare, Galium aparine, Matricaria inodora and Alopecurus myosuroides, by post-emergence application in an emerged crop of winter wheat.
  • a wettable powder was formed from:- by mixing the ingredients and.grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at a rate of 3 kg of wettable powder in 200 litres of spray fluid per hectare to control the growth of a wide spectrum of established broad-leafed weeds and grasses as hereinbefore described, for example Veronica persica, Viola arvcnsis, Stellaria media, Matricaria inodora, Polygonum spp., and Alopecurus myosuroides, by post-emergence application in an emerged crop of winter wheat.
  • a wettable powder was formed from:- by mixing the ingredients and grinding the mixture in a hammer-mill to give a wettable powder which may be diluted with water and applied at a rate of 5 kg of wettable powder in 200 litres of spray fluid per hectare to control the growth of a wide spectrum of broad-leafed weeds and grasses as hereinbefore described, for example Veronica persica, Viola arvensis, Stellaria media, Matricaria inodora, Polyqonum spp., and Alopecurus myosuroides, by post-emergence application in an emerged crop of winter wheat.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP81300430A 1980-02-05 1981-02-02 Herbicidal compositions comprising 1-(3,4-dichloro-benzyl)imidazole-N,N'-dimethyl-4,5-dicarboxamide Withdrawn EP0036244A1 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8003752 1980-02-05
GB8003752 1980-02-05
GB8007543 1980-03-05
GB8007543 1980-03-05

Publications (1)

Publication Number Publication Date
EP0036244A1 true EP0036244A1 (en) 1981-09-23

Family

ID=26274397

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81300430A Withdrawn EP0036244A1 (en) 1980-02-05 1981-02-02 Herbicidal compositions comprising 1-(3,4-dichloro-benzyl)imidazole-N,N'-dimethyl-4,5-dicarboxamide

Country Status (11)

Country Link
EP (1) EP0036244A1 (cs)
AU (1) AU6681381A (cs)
BR (1) BR8100615A (cs)
DK (1) DK45381A (cs)
FR (1) FR2474821A1 (cs)
GR (1) GR73854B (cs)
MA (1) MA19069A1 (cs)
OA (1) OA06737A (cs)
PL (1) PL229497A1 (cs)
PT (1) PT72437B (cs)
RO (1) RO81322B (cs)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2809022A1 (de) * 1977-03-04 1978-09-07 May & Baker Ltd Imidazol-derivate

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2809022A1 (de) * 1977-03-04 1978-09-07 May & Baker Ltd Imidazol-derivate

Also Published As

Publication number Publication date
PT72437B (en) 1982-01-29
MA19069A1 (fr) 1981-10-01
FR2474821A1 (fr) 1981-08-07
RO81322B (ro) 1983-02-28
RO81322A (ro) 1983-02-15
OA06737A (fr) 1982-06-30
PL229497A1 (cs) 1981-09-04
DK45381A (da) 1981-08-06
GR73854B (cs) 1984-05-07
BR8100615A (pt) 1981-08-18
AU6681381A (en) 1981-08-13
PT72437A (en) 1981-03-01

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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AK Designated contracting states

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STAA Information on the status of an ep patent application or granted ep patent

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18D Application deemed to be withdrawn

Effective date: 19820903

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Inventor name: HEWETT, RICHARD HENRY